Strictly Anonymous Confessions - 1529 - Joelle is Into Crossdressing, Facesitting, Pegging and More

Episode Date: July 24, 2026

Joelle is into crossdressing, facesitting pegging and more and he called in to talk all about it. Tune in toto hear all the details including when and where he started noticing  women’s undergarments, the first time he put on a pair of panties and what he enjoyed about wearing them and when he continued to wear them,  first wife and what he did and didn’t do secretly while married to her, the “whore phase” he went through after his divorce and the random women he would hook up with and what would go down, the couple he hooked up with and  what he did with the both of them including facesitting and trying a creampie,, how his new partner brought up pegging and anal beads and how he felt about it, how she found out his crossdressing and how she reacted, how he felt the first time he dressed up in front of her and what went down between them while he was dressed up, the night his wife put make up on him and they went out while he was fully dressed and why it was the hottest night for him, when he got into chastity and the longest time he’s ever been caged for, how he enjoys being a sub and the maid scenario he gets to live out once a week, how often he dresses up ow and what he enjoys wearing plus a whole lot more.  GET A COPY OF THE STRICTLY ANONYMOUS BOOK! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY HERE: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://amzn.to/4i7hBCd⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  or Pre-order audiobook version ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠   To see HOT pics of my female guests + hear anonymous confessions + get all the episodes early and AD FREE, join my Patreon! It's only $7 a month and you can cancel at any time. You can sign up here: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.patreon.com/StrictlyAnonymousPodcast⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and when you join, I'll throw in a complimentary link to my private Discord! To join SDC and get a FREE Trial! click here: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.sdc.com/?ref=37712⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ or go to SDC.com and use my code 37712 Want to be on the show? Email me at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠[e-mail]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ or go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠http://www.strictlyanonymouspodcast.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and click on "Be on the Show." Want to confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. All voices are changed.   Sponsors:   ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://LoadBoost.com⁠- To get 10% off LOAD BOOST by VB Health, use code: STRICTLY   ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bluechew.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Buy 2 months of Bluechew GOLD and get the third month FREE! Use code: STRICTLYANON⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠http://bollandbranch.com/strictlyanon⁠⁠⁠⁠⁠⁠⁠ Use code STRICTLYANON for 15% off ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://beduc.at/pd2626-anonymous⁠⁠⁠⁠⁠⁠ Click here to take the quiz and  get your personalized SUMMER roadmap to sexual happiness Follow me! Instagram  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/strictanonymous/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ X  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://twitter.com/strictanonymous?lang=en⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Website  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠http://www.strictlyanonymouspodcast.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Everything else: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://linktr.ee/Strictlyanonymouspodcast⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

My name is Peter Parker, but I'm also Spider-Man. This Thursday, we're faced with a threat. That can be anyone. The world may have forgotten Peter Parker. I'm just a neighbor, friendly neighbor. But he hasn't forgotten them. Sometimes Spider-Man has to do the hard thing. That's my responsibility.

Talk to Banner? I didn't know you could get that big. Spider-Man, brand-new day in theaters Thursday. Adipus Podcasts. Conversations with online strangers. We place ads online. The Craigslist is definitely like the gift that keeps on giving. Real people respond. You go to Santa for a Thailand. You can't not do it. The temptation is just too much. With real problems. Your friend know that you're banging her or no? No, he has no idea. And anything goes. Motto of the show, let your freak flag fly.

Probably the only good advice I'll ever give you is to rehide your whips and change. Here is your host, Kathy. Hey, welcome to the Strictly Anonymous podcast with Kathy. If you haven't followed the Strictly Anonymous podcast on Instagram or Twitter, follow me at Strict Anonymous. If you want to be on the show, it's called Strictly Anonymous because I keep everyone anonymous. I change people's voices. You can email me from a phony email, call me from a phony number.

I just want to hear your true story. And since this is a Fetish Friday episode, I love to hear your story about your unique fetish. Whatever you're into, if you got a fetish, you could be on the show. And if you have a pantyose fetish or a cross-dressing fetish and you call in, I will give you free access to my Patreon. Now, on my Patreon, I have two tiers, one for cross-dressers and one for hosers. Those are guys who like panty-hose.

On those tiers, you get every single episode, early ad-free, plus intro-free. Also, you get all the picks, anonymous picks of all of my guests, plus you get exclusive content over there. And since I've been doing this for many, many years over on Patreon, there's so much exclusive pantyhose fetish episodes and cross-dressing episodes that are only available on Patreon. The hoser tier is $8 a month. The cross-dressing tier is $10 a month because cross-dresses also get the hoser episodes as well. But if you call into my show, you're going to get a whole year free. So if you want to call into the show, because you have a fetish that you want to talk about, send me an email, strictly anonymous podcast at gmail.com, or go to my website, strictly anonymous

podcast.com and click on being the show. I do have a book out. It's called Strictly Anonymous Confession, Secret Sex Lives of Total Strangers. It's available on Amazon, an e-book, and audiobook, and paperback, but it is now available for an audiobook to pre-order. Okay, it's coming out August 25th. So it's coming out very soon. You could purchase that my book, by going into the description and clicking on the link. Now, anyone who calls into my show as well as anyone who buys my book, if you send me a screenshot of your purchase, I will give you free access to my Discord. My Discord is a super fun place.

And in there, there are so many different channels. You get to post whatever you want there, and everyone posts and talks to each other. And there's a whole community over there. It's private. It's free, but you could only get the link through me. I throw it in complimentary to anyone who calls into my show, joins my Patreon, or buys my book. So send me a screenshot of your picture to Strictly Anonymous Podcast at gmol.com. There is a lot of fetish and kink channels over on my Discord.

Okay, today I have on Joelle. Jewel is great. He's got a very interesting story because Joel is a cross jessor, but he's also into a lot of different things. He started out getting into like feminine undergarments when he was younger, wearing panties and then he got married. He wasn't allowed to do anything because he had a very vanilla wife, but he didn't do much when he was with her. But when they ended, when things ended with her, he went into something called his whore phase. And during his horror phase, we get his stories on a lot of other crazy things that he did that have nothing to do with

a crushessing. Like he hooked up with women, like in crazy scenarios, and then a couple, and he wound up having a hug up with a guy. And he was into face sitting and cream pies. And he got into that and then he got with another partner. They're not married, but they've been together forever. So it's kind of like a wife. And she was into pegging and anal beads and all that kind of stuff. And then she wound up catching, secretly dressing up. He had, and he talks about how she wound up catching him, how she reacted. And then what went down after, which is her, him dressing up in front of her, how he felt about that, how she felt. He talks about, you know, how. How she eventually like wound up giving him advice on the way he crossdresses and what he's wearing.

She eventually put makeup on him. They went out fully dressed one night and had a great time. He talks about like their intimate experiences together when he, he's dressed up. He's now able to cross dress what he wants. He's got this maid thing that he has every Thursday. He talks about that when he's the maid and he gets to dress up. Today is Thursday that we were taping. So he wasn't his maid outfit.

And he talks about what he was wearing. where he buys his clothes. He's very into chastity too, and he talks about that as well. So this is like a very interesting episode that has so much in it. His story is great. He's living in his best life. Let me tell you his second girl. It's like the girl of every crossdresser's dream.

Let me see here all about her because she's very accepting. And the whole episode is great. So I'm going to get right to be right back on with Joelle. This is the strictly anonymous podcast. Strictly Anonymous Podcast. Hi, Joelle. Welcome to the Strictly Anonymous podcast. How are you today? I'm doing good. Yourself? Good. I need to tell people what happened before we start TV because I was like, I hear you

breathing. Like it's very loud. Like blah, blah, blah. And you're like, well, I am wearing a corset. And so I can barely breathe. It's like, oh, my gosh, it's so fucking funny. I'm like, I need to tell everybody. Because you are dressed up for your call. You are a cross-dresser. You know, I want to get like your whole life story. You know, why don't we go all the way back to how you got into cross-dressing. You want to start there? I'm sure that's a long time ago. Sure.

Well, okay, so actually, like, physically cross-dressing full has probably been the past, I'd say eight years. Okay. But definitely, like, most everyone you talk to, and I think I even heard one of your more recent episodes, the cross-dresser. I don't know if it was on the exclusive or if it was on the public one. But, you know, he was talking about, like,

the old Sears and J.C. Penny catalogs. Oh, they all do. Oh, man. I don't know what it was, but seeing those models in their like corsets and especially like the, they had like the bridal lingerie section. And that was such a turn on. I'll tell you what it was. It was that there was no porn back then, right? There was, you know, unless you found your father's like Playboys under his bed or wherever he hit him if he was a good hider, you had no way of seeing anything nowadays you know they they see it walking down the street so the only way you would get a glimpse of a check was in those catalogs yeah so is it like feminine is it like women's undergormants that gets your interest right away oh yes yeah I was probably I don't know I can't I don't know the exact age where I really started there's probably like 13 you know typical puberty time frame

hitting and yeah just seeing that like and also lo and behold when they had like the uh i remember hearing like playtext cross your heart commercials on television like that's been forever ago but you know it was in seeing that on television was like like so like you know that was my only like sexual like thing i could have access to yeah you and uh tons of other guys i had a roommate that told me that he loved the catalog to look at women in bras. You know what I mean? I don't even think he was a crushessor that I know of, but I think a lot of guys,

whether you were interested in wearing it yourself or not, that's where you saw boobs. The most boobs you could see, you know? What was underneath all these women and girls walking around? And it just, like I said, like the, see the girls in their panties and bras, and you could see their, you know, tits smashed up or bigger than normal. And then definitely, I think the corset part really, you know, I didn't know it then. But, you know, that helped excellent, I don't know what's the word, accentuate the

female form, that hourglass look. Oh, yeah, that's what it's all about. That's why you're literally not breathing talking to me because it's making you look really. It's giving you the hourglass look. That's what it's for. As best as it can. You're doing good. You're doing good.

Okay. So you start noticing all that stuff. That's one thing to notice. Like I said, I had a roommate guy who said he used to look into the look at the bras, but he wasn't necessarily wearing. When do you start thinking, oh, like, I want to be those girls or I want to put that on? I mean, like, what comes next? I would say probably maybe, I don't know, 15 or 16 is when the first time I ever tried on

a pair of panties. And, of course, it's just like anybody else, it was my older sisters. Both my sisters are significantly older than me. So by my teenage years, they were out of the house. They were either one was starting their life, career, and the other one was still in college. So it's like kind of I was left alone, you know, great general, what do you call that? The Gen X story, the last key kid. Oh, yeah.

We were like, yeah, the way we treat our kids is very different than the way we got treated. We did whatever the fuck we wanted. And we were left alone a lot. So I remember my sister, she came home from college. and it was like spring break, and she was getting to do like, you know, the parents kind of let the leash out a little bit on her. She knew, they knew her friends. They let her go, but she had a lot of laundry left over.

And, you know, being the kid, I learned how to do laundry. And I was like, well, send the dirty clothes. I'll just clean it, you know. And then when I was done, I was, you know, I just like, I wonder what these feel like. So I put them on like any other young teenage kid does and just found it really exciting and, you know, very arousing. the same time. What was it that was arousing the feeling of it? Did you look at yourself in the mirror?

Definitely the feeling of it, yes. Like, I mean, because, you know, that's not like, once again, not like today, rear options were basically T-YD's, and it was such a different feel and escape than the normal. So, yeah, definitely, you know, I tried that on and, like I said, I could basically wear it, you know, whenever, because I knew my parents' schedules. Like, they both worked and I knew they were not going to come home before a certain time. It just never happened. I never got caught by my parents. Thank God.

For them? Not just for you, for them, you know, because that generation was just lived in denial anyway. Like they didn't want to fucking know anything. You know what I'm saying? Yes. So it's good. Oh, yes. And so it went on.

And then, of course, you know, my mom was a professional woman. So she wore the old, you know, the blouse, the skirt, the slip, the heat, the, the, the panty hose and I tried the panty hose on too and I just found that a lot of fun and luckily my mom and I um we were at the same height the same build like basically I am just a male version of her to a degree so you know when I finally hit like you know 17 18 I could try on I could actually fit her clothes were just the same as she did. And I could walk around her heels and her, it was just a lot of fun now. She had no corsets, unfortunately, so I didn't get to enjoy that as a young kid. But that happened. So that was definitely, I guess, the backstory and all, but also to put to probably more to the kink of

my life that I enjoy the most, the kinks I enjoy the most fetishes is, like you said, we didn't have, like, we didn't have, but we did that television form, but that was, you know, few and far between. But then I found a copy somewhere on the street. I grew up in a very major city on the East Coast. And I found a copy of penthouse variations. Oh, what was that? If you're familiar with that. No, I don't know. So it was like, it was like, what do you call that? Reader's digest size. But it had stories in it. Right. And these weren't the typical like just male and female. It was like, you know, VDSM cross-dressing, you know, forced by gangbangs. It was all of that.

It's like my show. Yes. Yeah, you're so. Yeah, I discovered your show about four years ago. It's been great. Yeah, there you got. You got the same variety, right? I got the same variety going down.

Yeah. But definitely I always found the stories of the guy being cross-dressed and being pegged or, you know, stuff like that was always the ones that turned me on the most. And even through like my early adult life, you know, once I left the house, I joined the military and I did 22 years. So a lot of that time, you know, the cross-dressing was repressed. Right. I didn't do it during any of that time, especially when I lived in the barracks. But even when I lived on my own, I really didn't do it just because I don't know.

Well, one, kind of busy for most of it, but yeah, I just never really did a lot of the cross-dressing. I still did enjoy the fetishes and the kinks. Like in your fantasy, you're reading about it. Right, exactly. In your mind. And maybe because you, listen, how old are you right now? I'm 51. Okay.

So maybe back then when you were on your own, like was Amazon around yet to just like buy shit and send to your house secretly? So maybe that's why you were. Well, it was. Oh, it was? Yeah, I mean, I came up, yeah, through the whole internet generation, you know, the dial up and all of that stuff. But I also got married younger.

So you're not by yourself. When you say living alone, you're not living alone. You're living with your wife. Yeah, I was living alone for a little bit, but then I got married. And that was, I mean, and then we're not together anymore. But like, definitely during that time, yeah, it was just, she, we did try. We did talk about some kinky things, but she was definitely not open to anything. But what were you doing?

Considering she not even in your life anymore, like what were you doing when came to cross-dressing through these years when you're, you know, now out of your parents' house, out of the barracks with a woman living with her, you know, are you secretly cross-dressing? Are you going all the way yet? Like, what do you do? No, I'm not, I'm secretly at most. I'm just playing with her panties. Oh, okay.

But you were playing with her panties secretly. Yes. Okay. Did she ever catch you? No, she never caught me. Okay. You know, but, you know, we did, I did try to bring up stuff. And you could just tell she was very like, no, this is, this is how it is. This is sex is just for like a little bit of pleasure, but mainly for having kids. And I was like, oh, okay, you know. And so, you know, I really did love her. And but we did just eventually grow apart. Okay, listen, like at a certain age, you realize that, like, sleep isn't a luxury anymore. It is a necessity if you actually want to feel. feel good the next day. I don't know about you, but if I don't sleep well, you know, I feel it the next day.

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And life was just different, so we divorced. Okay. Did you ever get remarried? Not technically married, but I have been with the same woman right now for 10 years, the past 10 years. Okay, so we'll get to her. So, but let's go back to like after your divorce and now you're living on your own. How old were you at that time? Are you still only like 25 or 30? I was, 17, 27. I'm doing all the, that's real fast. Around, like was it late 20? I was 39, 39 when I was divorced. Oh, so you stayed with her for a long. You stayed with that wife for a long time.

Oh, yeah, 18 years. Oh my God. Okay. So, so. 18 years, all you're doing is like kind of reading, probably Googling about it, but also wearing her panties, but nothing further than that. No bras, no legate, like no, like no pantyos, no lingerie. Nope. Okay. Okay. Because. She would have known, she would have found it. And I knew better than to deal with that.

Like, she did find a porn magazine once, and that created a whole issue and a whole long-term deal. just a mess with, it just created a lot of friction. Yeah, it's not ridiculous. It's like, it is. Yeah, but anyway, go on. So I just learned to like not even try to hide it because if I did, it would just be found and it was not worth the headache to go along with it. And you would lose your family.

I'm assuming you had kids with her? Yes. Yeah, so you don't want to lose all of that stuff. Okay, so you were, listen, I give you credit. Some people can't fucking control themselves, but you really didn't want to get caught, so you kept it at a minimum for all that time. but now that you get divorced, what goes down? Oh, I hit the horror stage.

Oh, let me tell you, I hit the whore stage. You made up for it. Oh, yeah, I made up for it. You're saying horror. You're saying horror phase, right? Oh, yes, the horror, yes, slut phase, whatever you want to call. Yeah, okay. Joel, the slut.

And that's back, you know, like you said, Craigslist was wild, of the wild time back then and also KIC was one of the newer messenger apps and it actually at that time it had video chatting which it doesn't have which really sucks so I would just meet all kinds of different people

in the area I lived in and what kind of people are you meeting? First I've met this this woman and she was pretty much in a, like, I wouldn't say sexless marriage, but it was only when her husband, who was a complete dick, he only wanted to do it, or if it was like a threesome, he would set it up

with who he wanted, like, she never got any real input into it. And so she was just like, I just want someone to eat my pussy. That's all I want. I was like, oh, I'm down for that. I love it. And that was one of my things my ex did not like. She did not like, or, And I'm like, what the fuck? Why do you not? Yeah. And so I met up with her. And the first time we met was at her place.

But she was like, hey, we got to go into this little like a she shed she had. She goes because her sons were in the main house and her husband was gone for some whatever weekend thing. So I'm like, I don't care. I'm getting some. She's getting some. And so, you know, went down to the deed with her, had fun. She was a squirder. And oh, my God, that turned me on.

even more. But she was like, okay, I got to go back in. And I'm left there, you know, hard as hard as a rock. So, you know, whatever, go home. I go back to my little place and just jack off and enjoy that one. And then it just became like, let's see what I can find. I learned it is insane. I just got on Craig's listen and put ads out myself like not looking for much in return, not looking to fuck. I just want to eat pussy and ass. That's it. And it is amazing, like click, click, click, click, kept hitting. Oh, yeah. Who was responding to you?

Because it's not just women, right? It's more guys, right? Well, I wasn't as a, I was just a guy doing stuff. I was just having fun with sex. No, I know, but I would still assume on Craigslist as, you know, guys, there's more guys on than women that you probably did get hit up by dudes now, or dudes pretending they were girls. Probably, but then you're like, hey, okay, I'm right now.

I'm down to do this. Let's go meet. And of course, that was probably the guys. But the ones who were, you know, basically we would find out, hey, we both had kick and we'd get on kick and we would sit and talk back and forth and be like, okay, let's meet up. Let's do this. And we would. And, you know, someone would come over to my place. Wow. Someone would go to theirs. It's pretty incredible your story. It's more interesting because it's not like, because I don't know what was going on in your town and your Craigslist, but typically, you know, a lot of guys don't find a lot of women on there. show started during the Craigslist days, you know, so I know all about it. So it's surprising to me that you had, you know, a fair amount of women responding and women in action with women from your ads, you know? Well, to be fair, I was still living in the same area where I retired

out of the military from. And it is, it's the largest army base in the United States. And so, like, you know, a couple of 10, Austin, Texas was only an hour away. So, like, and in Texas you can drive, you know, driving four hours and coming back on the same night's not unheard of. It's a big state. So, you know, I would go and a lot of these women were like, their husbands were deployed or their, right. That's where I thought you were going.

Yeah. Okay. So that's the key. That's the key to get in checks. Yeah, there's a lot of, I'm sorry to keep kind of going on. No, because no other town except one of the. of those, are you going to get all those women emailing you? I'm just sorry. It's just

not the norm. 100%. I'm not like, I know I'm not the most handsome guy. No, no, no, no, no. It doesn't matter if you were a fucking 10 or a 12, that has nothing to do with it. There's just not that many women in places doing that. But when you have a small place

where all these women, like you said, their husbands are deployed, you got a lot of, you know, it makes sense that it's the location. That was the difference. It makes sense. It's interesting. I'm glad I asked because that's kind of, Craigslist doesn't exist anymore, but, you know, that would have been a great tip to some people.

So go on with your story. So you're just hooking up with women at this point. So what goes down? Eventually I meet, I'm talking to this one woman. She's like, well, I really like, she goes, would you be interested in, like my husband giving you a blowjog or are you fucking him? Oh.

And I'm like, well, as long as I get to eat your pussy, I guess I can deal with some, we can try it us and see how I like it. So, you know, let's say we go over there. We all, well, we meet at a restaurant the first time. Like I was got to that point where I'm like, I'm just not randomly running into someone's house. Because I got lucky, like I had no issues, but like there was a couple times like it kind of fell off. You know what I mean? Like the whole, just something felt weird.

So I was like, okay, I'm not going. I was pulled up to one person's house and I knew something felt weird. I'm like, I don't know what's going on. I'm not going to risk this. I'm done. I'm out. and I left. So, you know, I never talked to that lady again, but, you know, quite possibly could have been fine, but I just, what I didn't think it was worth of risk. And then I started like,

well, if this lady and her husband want to do this, I'm willing to try it, but I want to meet them first. Like, I was not going to get set up in some situation. Okay. So we met and we met, we had dinner together and drank and all. And it was a lot of fun. And they sat together at first and then she went up to go to the bathroom and him and I were just talking we got along great and then so she sat next to me and there was a little bit of touching and feeling going on you know my feeling her leg her feeling me up and then her and her husband switched and he was feeling me up and like okay this is different but i don't like i'm not opposed to it like it's i'm not freaked out by it at all yeah so then we're like okay let's cool like so when your schedules and aren't my schedule work

we can meet up and like we can you guys want to get a hotel we can get a hotel you know if your place whatever so the first time we met up was at a hotel and it was a lot of fun and you know through our talks you know she definitely found out I had a kink for a face sitting where I like to just lay down and a woman get on top and she can grind her pussy and ass on me and on my mouth any way she wants you know let her have the control and that's what I found out I like the not being control. Right. Kind of being smothered a little bit, face sitting, right? Yeah. Yeah. All of that. Okay. So I lay down. She sat on my face and all that. And she's me and her just started out of 69 and her husband watched them. She got up. I could definitely

tell by, you know, the pressure and the weight shift that. And then her husband started blowing me. I'm like, oh, feels good. I'm not having a problem with this. And we're having good. It was a good night. I end up coming in his mouth and she comes on my face and he ends up fucking her. and I've always read about cream pie eating. I'm like, fuck it, I'm doing this. Like, this is your whore face.

It is. I'm like, this is my first chance ever to do this. And I was like, yeah, I want to eat you now. She's like, okay.

So she laid on the edge of the bed. I got there and I got to, and it was just great. I enjoyed it. So played with them for a good while. And I didn't end up topping him. I ended up sucking him. And that's about as far as I ever went with him and her and I fucked a lot.

Even, you know, there's a lot of normal stories with that. But never, it never got the cross-dressing or anything. It was just me like, hey, I do not mind a little bit of bisexuality. It does not bother me a bit. I enjoyed it. And then so life changed and I ended up moving out of that area. So definitely that well is run dry. but I end up meeting my current partner.

We call each other husband and wife to everyone because it's just easier. Okay. But we've lived together, you know, for, you know, we've known each other for 10. We've lived together for 8. And at the beginning, she knew nothing of all of the cross-dressing or the kinks. Right. But that has come out over time.

How? And, well, let's see. Because she was married and divorced also, and she was kind of, she wasn't quite going through her hor phase as much as I was. But she just enjoyed the, she's the pillow princess any day of the week. It works perfect for me. Because you love that, yeah. I love that and then everything else.

But, you know, one time we were just playing around and she was giving me a blowjob. And then she's like rubbing her hands. then she just touched my ass. I was like, oh, that feels good. And she was like, that doesn't bother. I'm like, yeah, it feels good. You know, so things went on and on. And then finally, you know, she didn't do much more than just play around the outside. And then we're driving one day and she's like, would you mind if I set the anal beads of your ass while I'm blowing you? And I'm like, hell no. I'm like, oh my God. So, you know, instant hard on. But she's thinking, this is, this is turning him on. And I'm like, oh, my God. This is back to those penthouse variation days. I'm like, I'm finally finding it. woman who's a little more controlling. Like, this was great, you know? Yeah. So, you know, we do that. That's fun and enjoyable.

Definitely a different sensation. And, you know, we're going on and on. And then she was like, she goes, I don't know, I really never knew how we got to these conversations, but she was talking one time. She was like, would you ever like to get pegged? And I'm like, and so she knew the term, which means she had some history or thought of it. And I'm like, yeah, I'm willing to try that in my brain. I'm like, yes, you know, that old cartoon cat with the eyes bugging out, all that

craziness that's going on in my brain. But I'm trying to play it cool. Like, because she only sees me as more of the alpha male type at that point. You know, I was, I'm a manager at where I work. So that's all she ever sees is me in control making things happen and things get done. You know, so that's all she ever really sees. So that's, and she knew, and she knew about my army life. So, you know, that's how she sees me.

But I'm like, hell yes. Finally, you know, jackpot, ding, ding, you know, all the nickels. Totally. And so it takes some time and she does do it. And I did enjoy it. I don't know if she enjoyed it, but like, it's like you said, she said it. And other people say, like, it's fun to watch. But like, there's no, like, real feeling, I guess,

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And so the way the cross-dressing part comes out is I went away for a business trip. I'm in a room. I'm in a room by myself and I'm like and I knew there was a lingerie store down the street I'm like screw it I'm just going to go down there so I go down there I buy like a body stocking I buy a small dildo and I buy a corset there and I go there I'm having fun my whole week there enjoying this everything and I come home and I just threw all that stuff away like oh she's never going to see and a fun. You know, I spent $100 some dollars. I got my enjoyment out of it.

Life is good. Right. But it's a secret. Yeah. It's still a secret. Yeah. And she finds out because this idiot here left a receipt in his wallet. And it was like sticking out.

Like, so I just threw my wallet on the nightstand like I normally do. And she just saw that. And so she was like, what's that? And she looked at it and she, and I had the day off. And she's like, what is this? Who did you buy this? this for. Like I bought it for nobody. I bought it for myself. And at first she was like, yeah, whatever, you know, typically, I understand. She doesn't believe I'm like, look, I bought it for

myself. Like, I did not buy it for some other woman, did not mess around with some other woman, you know, because one Craigslist isn't around. And I'm at the hotel with like other people in the company I'm in. So I don't need them to see some random woman coming in and out. So I'm like, I know to play it a little safer that way, because you don't shit where you eat. you know yeah so and she's like whatever like yeah she goes and so she and I guess she was pissed and she's like well do you have it and I'm like no I threw it all the way she goes oh you gave it away I'm like no I threw it away I bought it for myself I did this every night generally after you and I talked on the phone I would just have fun and then I'd go to sleep and next day dude like just repeat

the whole process and she was like fine whatever I have to go to work and so she She goes to work. And she sends me a text. She goes, if that was really you, I want to see you when something likes at. And I'm like, she goes, when I get home. Interesting. So it's like, crap. This is like the girl of your dreams, though, kind of.

Yes. Yes. So it's like quick. Google, do, do, do. I get Google up and I'm looking around. And it's like nearest lingerie store and all this. And like, oh, there's an hour away as an adult store near it near the airport, which they always seem to be by. So I'm like, well, let me cruise, cruise down there.

I buy some things. I come back home. I have them on. And it was really weird the first time. She came home and she's like, well, let's see. It was really weird being in lingerie for the first time in front of somebody else. I could imagine. So I was nervous.

I didn't know what to say. And you could just see she was like, you know, just looking at, you know, like, okay, this is different. like all right and you're wearing what are you wearing by the way i'm wearing like a body just a body stocking one they go but it was crotchless so you know we can cover the legs the chest and the arms and i had a corset on and i think she was impressed i could i could get a corset on right i can imagine because by yourself it is a lot more difficult than people agree right people would even know So she's like, okay, and what do you like to do in this? And I'm like, well, I would love to, you know, go down on you.

And she's like, okay, that can happen. And she goes, and so I'm going down on her and she's talking to me and she flips over. And she goes, well, now I worship my ass. So I'm playing with her ass and having all that fun. And she goes, okay, it's time for your ass. And like, okay, she goes, lay down, get a doggy position. And I can feel the cold loo hit. And then she just slams, she grabbed one of her dildos out and just slammed it into me.

And I was like, okay, you know better. You know, I'm like. How was she getting you back? Well, no, because I've always wanted a triangle with her, but she is like, she doesn't mind like a finger or my tongue. But she's like, no, no toys. Your cock is way too big for my ass. So I'm like, okay, you know, what I enjoy. the most I'm getting to do. I'm not complaining about not getting to stick my dick in her ass at all.

But I'm just like, you know, I'm like, so I'm like, do you not know better? Like, you don't like when I just shove my dick up your, up your pussy. Like, what do you think this is any different? Yeah. So she's like, okay, let me try this again. So then she slowly works it in and out this time. I don't know if she was just mad at me about catching me. And that was her way to get back at me. Probably was. But, you know, she was like, okay, you know, all right. She goes, when we were done, she was like, just changed. And she goes, let me just process this, you know, for a while. And then, of course, the typical questions come up like she goes, are you gay?

I'm like, no, I'm not gay. Really, I'm not. She goes, well, are you bisexual? And I'm like, and that's when I tell her, like, you know, I have hooked up with guys before. And I go, I have sucked cocks before. And, you know, she was like, well, tell me some of those stories. I tell her about them and she's like, have you, since me and you have been together, have you cheated on me?

And it's like, no. She goes, guy or girl, like, no. Like, it's all been this. And she's like, okay. So luckily about the same time I got caught and all, that's when like the big, what do you want to call it, like T, Tmu explosion hit. So you could buy stuff super cheap to see how it fit or how it worked. And definitely, like, it's good for like trying some like niche things,

but like that's not where definitely there's stores that cater to cross-dressors and because you know men have different sizes and proportions and so finding women's clothes to actually fit and look good is a lot more difficult right so there I have discovered some of those different stores that do cater to what are the names do you want to I don't know you don't know but they're there on Timo is what they are there you find them you just Google you just Google uh cross-dress are closed men. And then, like, certain sites will hit up.

And, like, you do pay a little, a premium for the specialty service. But once you figure out their, like, measurement system and all, it's worth it. Because you're not buying something that, oh, I can't fit into this. Because definitely there's websites that are like, oh, yeah, you know, this is a little women's, like, extra extra large to XL. I put it on. And it's like, I can't even close the thing around me. Wow.

And it's like, there's no way, like. So definitely a lot of trial in air and learning to close. So over the years, you know, it's gotten to be like, well, let's try it on. Let me see. And so she'll be like, you look like a train wreck. She'll either tell me I look good, like, okay, that outfit, that works. That's a good, complete outfit. Or she'll be like, that's just, that's just a mess.

She like helps you out. She's like, right? She does. Yeah. Yes. Yes. And so she has taught me how to do. do makeup and I am okay at it. But she definitely has done makeup for me where, of course,

you know, she makes it look good and right. So the first time she ever did my makeup, she was like, hey, what do you want to do for your birthday? And I have one of those great birthdays that's in between Thanksgiving and Christmas. So, and I'm like, I don't want you to buy me anything. I go, I just want us to go on a little vacation. And I go, I want to go out one night, fully dressed, me and you. And so we went to a casino of Vegas. So, you know, you can be cross-dressed public there and nobody's going to care. Because there's enough other freaky shit walking up and down the streets that no one's going to freak out about.

Yeah. And it's far enough away from where we live. You know, the chance of us running into somebody is slim. So we go. We just enjoy our first few days at the casino. And I, and she's like, okay. tonight's the night. Are you ready? I'm like, yeah, I'm ready. So I go through, pick out the outfit. She looks there. She goes, okay, yeah. She goes, we need to go get a few more things to make it better.

So we go get like, you know, this is smaller things, like the jewelry, the things that make it look, you know, push the looking from good to looking great. So we get all that together and get dressed up. I'd shave, put the dress on, put the breast, put the breast forms on, the corset on, the heels, the stockings, the full, the full thing, you know, the JC Penning Catalog come to life. Yeah. And the dress and then the wig and she does my makeup. And she was like, and by this point my mom has already passed and she goes, oh my goodness, you look just like your mom.

Wow. I'm like, I don't know if that's a good thing or a bad thing. But she. You did say your carbon copy of her. Yeah. and so I'm like okay she goes well let's go you know she got dressed up looking good and too we just had fun walking around the casinos

playing the games and she was generally always buying me but she'd be like hey go get some drinks so I'd go get drinks and come back and I think she I think she did enjoy me being out like that and it was nice having her with me so you know things did get uncomfortable at least I had somebody who I trusted next to me

me. So we just, that was the first time everyone went out. It was a lot of fun. Then we just go back to the room and we have a lot of fun with, you know, then we just pull around. And her in, like, I would rather see a woman in lingerie than I would rather than see a woman naked. Right. Just me. Yeah. And I know a lot of guys are like that. Yeah. And having, having sex with her while we're both, like, in lingerie, was one of the sexiest things ever. So great birthday to me. That was the first time? The first time her and I had sex together, both dressed up. Yeah, perfect.

Okay, cool. Yes. And so, you know, and after that, you know, that's when we, I found your podcast a little bit before that, but then we started, like on long drives, we definitely listened to it. That's the great thing about media now. I don't have to listen to it. You know, you don't have to plan your life around when you're going to watch or listen to something. Yeah, it's great, right? I can't believe it took you this long to call in.

Has your wife... I've been listening to you for about five or six years. Yeah, yeah. Has your wife ever given you like a free pat? Like she knows you're into guys, right? Have you ever like... I mean, I'm assuming she mocks it up when she pegs you and everything. So, and you're not a cheater, so you're not going to do anything about it.

Has she ever talked about you being with a guy or wondered if you have that urge because you have done it in the past? But I'm assuming you haven't while you're with her, correct? No. I have not while I was with her. I have talked to her. Like, we've talked about it. And it's like, I'm like, I don't ever find a guy like in day-to-day life attractive. But like, a dick, yeah, it's fun. You know, when I did suck a dick, it was a lot of fun having one of my mouth here and me be able to get that guy off. Right. So, which is really weird because like sexually I don't want to be in charge of anything. I just want to be submissive. Yeah, interesting. So, and I brought that up to her and like we've tried some like Femdom weekends or like some things and it's it's harder, I think for her to grasp the whole concept or get into that space, that mind space. But that's okay with you, right? Because you're fine with like everything that you have at home, I'm assuming.

Yes. Because like you said, it's not like you're the type of guy that's into guys when they're walking around. It's more so like if it's in the moment it's there, you'll go for it. But it's not like something that you're craving. Is that correct? That is correct. Yeah, definitely not craving. No.

Yeah, interesting. And so how, like, what's your routine now? Like, does she dress up a lot in lingerie after like you realize you love that so much? Is that something that happens once in a blue moon? Oh, no, that happens often. She knows definitely when she knew early on that I, like lingerie, like her in lingerie. Yeah.

And she's what would be called a BBW. And, you know, just her skin is soft. She looks cute in her different lingerie outfits and it turns me on. Right. And she knows it. But then, you know, age hits up to every guy and Blue True does wonders. But my biggest issue is not getting hard. It's just the fact that now for some reason my sexual endurance is nowhere near

what it used to be. Interesting. Why do you think? By the way, have you tried? By the way, have you tried Bluetooth gold? No, I have and I have heard it. I might contact. Yeah, you should upgrade because let me tell you. And you could get like your third month free through my sponsorship or use my code. Let me just tell you I, you know, because I can't take some of these products that I advertise. So I always look to other people to tell me, right? Because I'm not, I don't want to sell shit to people that's garbage.

You know, Blue Chew, I love it. But Blue Chewold, you know, know, I had Adam buy it to use it and like, let me just tell you a guy on my discord, or my Discord or my Patreon popped in recently and said he used it. And he couldn't believe how horny it made him. Because it works on your mind too. And he said he was doing it like the next day he was still horny and wanting to bang his wife. It says it's not just like getting you up and hard. It's also dealing with the mental thing. So maybe see if that changes things for you. It's not about endurance, but for some reason he was saying like that was his experience, that he was still like he did it so many more times.

He was still horny the next day. Like, you know what I mean? That's what he said. So try, upgrade and see the difference, see if that helps anything. Okay, I'll try that. Yeah, definitely I'll let you know. Yeah, let me know. I love it.

Yeah, go on. So definitely because I don't last as long, but luckily I enjoy oral and she enjoys receiving oil, that it still works out that I can get her off. You could tell like she's not getting off by me penetrating her all the time. and she's not really ever expressed interest in like hotwifing or anything like that. I have let her know like I would have no problem with you having sex with another guy to help you get off. But she hasn't.

And, you know, I'm not going to push that area because once again, we're both. Yeah. We're both in our 50s. We're both like, like our kids are grown and on their own. So we can have some fun. But like I also know like it's not it's not worth pushing an issue. why it might happen one day down the road, but if I push the issue, it'll probably never happen.

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Expertly mixed coquered. A perfect pairing for an evening with good company. Please enjoy responsibly. Must be 19 plus. Right. Right. Well, you know, listen, if you listen to my show and you hear all these guys that sometimes eventually do get the wives to do it, it is a matter of playing the long

game, you know what I mean? For sure. You know, there are things you can include in your daily life that might lead to it, like what guys typically start with is just like the role playing. You know what I mean? when you're together. And that could maybe help like satisfying her too

if, you know, getting toys and pretending that another guy is there with you. We've done that. Yeah. We've done it to a degree like where I told her like, you know, you know, so we were on like a trip

and we stopped at a rest area like 15 minutes before we would get home. And I fucked her, came in her pussy. And then when we got home, the fact that like we got home and like her, she had a cum-filled pussy that I went down on was, was a lot of fun. Like, it was great. Right.

Because it kind of, and she knew that, and like, it kind of was a role-playing scenario. Yeah, that's kind of hot role-play scenario. Smart. Yeah. Yeah. Yeah. Like cream pie, but yours, but it's pretending it's another guys, right? Mm-hmm.

Yeah. And then along with the fandom, we got into, I'm, I do enjoy Chastity play. Okay. I don't have a small dick, but, like, I finally did find that, you know, once again, when you research and you find something that will fit better and build better that accommodates your size, like, I've worn, I think you had, you had the guy on your show and I ordered through him. And, you know, it was like, this was no like $50, $60, you know, this was a couple hundred dollar cock cage, but it was metal and it was built to what my, my penis is, you know, in its

normal state. So I could wear it around a lot more comfortably all the time. Right, because I remember somebody recently saying that the key to being comfortable in one is you don't want any room to grow, right? Right? Isn't that true? Yes. Because you don't want to be able to grow and then it's pushing and it's hard. Like it has to be like no space. And I would have never thought of that. Or maybe it's the opposite. I forget. Now for me, like mine, when I'm soft, it fills it. It fills it. Right. I think that's what it's supposed to be. Right. When you get hard and excited, of course, it, like, it, like, the girthiness expands. Yeah. A little bit. And it comes around the bars. But, like, it also kind of will pull up on your balls and they get tighter, too.

So there's a little bit of, not like, a pain. Like, it's a pleasurable pain. Yeah. You know, it's not like, oh, this hurts. It's like, it's not killing you. It's like, oh, this feels good. But you can still, you know, do day-to-day life stuff in it. And I have worn that. that I would take it off every day just like for hygiene clean like during a shower clean myself real good and clean the cage real good because you don't want anything funky. And but she does she has enjoyed that. How long have you worn it for? How long total? The longest. The longest I ever wore on one time was three months. Wow. But like I said, I would take it off daily when I took a shower to clean. Yeah, of course. Right. But then we've been I guess in playing with Chassely on and off for like

three years. And so it's kind of fun. Like she does have like a necklace and she'll wear the key when we're like out of town. And I've told him, she's just wear that around town someday. And like, I even got her like a t-shirt that says, it looks like an everyday t-shirt, you know, like some crazy print you buy the, you know, like girly print. Like you buy a cracker barrel or some shit like that. And but it says key holder. Yeah. And I'm like, just wear that around town. Or if wear one of your dresses and, you know, because she's got big, big boobs. I'm like, you know, wear the bra that makes your boobs look even bigger. Wear that key, the key around your neck.

She goes, well, what if someone sees it? I'm like, well, what if they do? Like either one, they're just going to be like, oh, that's different or two, they're going to know what it is. Like, you know. Right. And I'm like, and if someone knows what it is, guess what? You know, and they know that you both know what it is. So they're not going to probably, you know, I've learned in life, you know, when,

certain people know certain things about each other and they're both quote into it or guilty of it, they're not going to help you because they know they're going to help themselves. Of course, yeah. That's why we did things with our friends growing up. You know, I had that guild by association. No one's going to talk because they'd be having themselves.

No Facebook or anything to bust me when I was a kid. Yeah. So, you know, so we did have done with some chastity play. And I wish she would be a little more femme domi and more of the keyholder aspect like publicly a little more but you know she's not comfortable with it and I have told we have talks you know pretty regularly like I would like you to do this but I understand you're not comfortable because she does have a very public job here in the city yeah you got to be careful with stuff like that I get it yeah so that's what like usually

if we go on a vacation somewhere we can indulge in this a little more which I'm sure is 99% of the time with every couple how much do you indulge in your cross-dressing at this point? So I have a pretty, for the world I work in, it is very chaotic. People have a lot of shifting schedules, but I have a set schedule, which is great. So I have every Thursday I have off. So when you sent the call to be like, hey, can you do it on Thursday? I'm like, perfect. You know, I can do Thursday. Right. So every Thursday, I basically, she goes to work and that's when I get to do what we end up calling the maid, the maids here to clean the apartment, do the laundry, do all of stuff. And it's just, and it's, she knows it's me being cross-dressed. And I do all of that

stuff while I'm, I clean the whole apartment, do all the laundry and. What are you wearing? Maid outfit? What's that? What are you wearing? Are you wearing a maid outfit or are you just wearing whatever? No, I'm wearing, I'm just cross-dressed. Right. But we just call it the maid because all the cleaning gets done. Because you like to clean. That's like a submissive thing to do, correct? Yes. Yes. It definitely ties into being submissive. And also, even with my work, because I usually work either, I'll end up working overnight or I'll work early in the morning. So I'm generally always off in the afternoon. So I always do the cooking. So that's kind of a, I don't know, that's always played into that, like submissive side of me. Like, I like making good dinners for her.

Yeah, that's fun. But what do you typically, like right now you're do it, you're the maid and you're in a corset. And what else? I got a corset on. I got the, you know, the breastplate on. So I got the corset on and I got some fishnets on and some heels. And then I just have a kind of a like mid-calf length pencil skirt and then just a long sleeve top on. And then just some jewelry to go with it. Do you like that whole vibe because that's how like your mom dressed for work back in

a day? Like, is that like the kind of gear you like to wear when you're fully dressed by any chance? I can do either or. Like, I can do classy and I can do slutty and I enjoy it either. Oh, interesting. Okay, that's fun. As long as it looks together. As long as it looks like together. Like, I've learned to appreciate complete outfits and definitely the whole cross-dressing routine, like I now understand why it takes a woman a while to get ready to go somewhere. That's what they all say. You have a new appreciation, right? I definitely do. Like, you know, now it's just like, you know, before we'd be like, hey, we need to leave

at this time. And over these, like, past, you know, years have evolved. It's been like, hey, I know we're going somewhere and you have to get ready. So you probably need to start getting ready around this time because it would be good to leave around this time. And she appreciates that a whole lot more. You can tell. It's not like we've got to leave by now.

Right. So it definitely has helped. and just relationship, you know, just small things like that. But, you know, both every day to day relationship and sexual relationship. Yeah, it's the cross-dressing has definitely been, it's fun to learn. And with the other day, she was like,

this just isn't a face for you, is it like, no, this is, because we went to a costume shop when they had like all these corsets on Iraq. And these are like not cheap every day. Like, you can tell these are like some vintage corsets. So I'm like, oh, these are awesome. So you just have fun looking at them. But she's totally down and cool with it.

Does she like to, like, do you dressed up intimately with her sometimes still? Sometimes. It doesn't happen often. But, I mean, it does happen from time to time. Right. But it doesn't really have to happen for you, right? Because it's not like you're not allowed to dress up. You have plenty of time to, like, fulfill your fetished fantasies, right?

Whenever you feel like it. without getting caught or anything. Yeah. And she doesn't mind like, like, oh my God. I discovered years ago, like leggings, tight leggings, like athletic pants. Oh my God, those are the most comfortable things. You like them? I'm wearing them right now.

I love wearing them just around the house. I have like quite a few pair. And she's fine with me putting them on and wearing them around. Like, you know, that doesn't bother her a bit. So I think she might be a little jealous that I do walk better in heels than she does. Hilarious. Yeah. How often do you fully dress and do the makeup and stuff? Was it only that time that you went out?

We've gone out a couple times that I've done it like that. And on, like I said, on Thursdays when she's at work, I generally do myself all the way up. As soon as she leaves and we say goodbye in the morning, that's when I get into, I go from my guy formed to Joelle and I just enjoyed the day. Well, that's why you wound up calling in Joel at your time because this is your day and your time to be addressed. Yeah. So everyone else, all you cross-dressers, okay, we're ending the podcast and this is what I got to say. You're going to get free year to Patreon. If you're a member, you just have to cancel your membership or let it run out if you bought a whole year. You know what I mean? And you will then, because you can't use the free

year when you're a member. You need to, if you're doing a, a monthly, cancel it, wait till the end of the month it wears out for whenever you paid for and then you could use it and you'll get a whole free year. Or if you paid for a year, just wait till that year is up and you could use that and get another free year. But for everyone, and I say this now, any cross jester or hoser, guy who's into panty hos that wants to come on the show and tell their story. I give you a whole free year to my Patreon. If you're a crosschester, you get a cross chest here. It's $10 a month. So it's like $120.20 you're getting. I don't pay anyone else to be on my show, okay?

But if you got a fetish, I'll give you free access, which I think is a great deal. But this is why you called in because I always make jokes that no fucking cross-dresser calls in because they make, you know, they're listening to my episodes when they're fully dressed. That's when they're looking for. You know, they make their appointment.

I'm booked very far in advance because I have a lot of people calling in. And so by the time that day comes, they're not dressed anymore. And they just flake. And it's so fucking irritating. So if you're a cross-dresser and you want to call in, working around your cross-dressing schedule like you did that's the reason why I didn't have to work around that you just scheduled it for this time and I was like oh perfect yeah Thursday yeah it's like perfect it's if you would have been like hey can we like I would have told you like hey my life

schedule doesn't allow for this but we could probably do it at this time yeah yeah we would have come to some negotiation yeah I typically don't negotiate with people because I don't have time for it but because I need cross-dressers because they're always flaking and even people with regular fetishes flake all the time. It is by far the one group of people that flake. Nobody else really does, you know, when they book a call for me. But I'm always looking for people to call in for the Fetish Fridays series. I love your story because it's like a little mix of a lot of things that I talk about on my show. We got, you know, we got cross-dressing. We have, you know, the lingerie fetish. We have face sitting. We have cream pies. We have Craigslist hookups. We have bisexual hookups.

A little bit going on there. We got a little chastity and Fem-Dom faces. sitting, right? We said that already. And then we have the whole thing with your wife accepting your cross-dressing. So I love it. I'm so glad you finally called it, you know. You have a great story, and it's going to be up this Friday. So stay tuned. All right. Thanks so much, Joelle, for calling in. And if you want to send picks, you know the deal. Send them now to my Patreon. Okay, cool. Thanks for calling it. You too. Bye. Bye. Bye. Recently, our company's softball team lost the big game by one run. Then Dale tried to console us with The quote, winning isn't everything.

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It's devilishly good. Red Bull, eh? Oh, that tastes heavenly. But, but what's this? Oh, dear. I forgot about that. Wings? Wings.

I can't have wings. Not at my position. Red Bull gives you wings. Okay, I just want to tell you before you go that my book, It's called Strictly Anonymous Confession. Secret Sex Lives of Total Strangers is now available not only in paperback and e-book,

but you can pre-order the audiobook. It's still not going to be out until August 25th, but you can pre-order it. The book is basically 17 different stories taken from my show. I kind of picked one story from each category that I talk about

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but you could pre-order it now. And if you buy my book in any format or pre-order it, I will throw in a complimentary link to my Discord. My Discord does not disappoint, okay? There's no way you get into my Discord any other way than getting the link from me, okay? I, give it to people who buy my book. There's tons of people in there. Everybody shares content with each other and that's what you get to do there. You could post your own pictures and videos. There's tons of channels. We have lots of contests where you can win a lot of money. It's a super fun place to be. It's a total strictly anonymous community and you will love it. I will be giving anyone who buys my book access to my Discord. It's private. Like I said,

all you got to do is email me a screenshot of your purchase, whether you did the audiobook. ebook or the paperback. Send it to me at Strictly Anonymous Podcast at gmail.com. That's Strictly Anonymous Podcast at gmail.com. And I will send you the link to Discord. So anyway, thanks so much for tuning in. This is the Strictly Anonymous Podcast. Strictly Anonymous Podcast.